Started out with an Atari as a young child, not even sure when and how we got it, but I had fun with it. When that broke we got a Coleco-vision system with the Atari attachment, since it made more sense to get a "better" system and use the attachment to play all the games we already owned. I won a Nintendo Entertainment System in a raffle in 4th grade, the one that game with R.O.B. and a Zapper with Gyromite and Duck Hunt (never actually owned or finished the original SMB). Got one of the original Game Boy bricks sometime after that because a friend had one and it was fun.
Years later, at a friend's birthday party, I played Final Fantasy 2(4) and knew I had to have that. So I upgraded to a SNES on Christmas the year it came out.
In high school I got my first computer, a 386, and then a 486 we picked up from one of my dad's co-workers a year or so later.
Things stayed like this until going away to college, where I got a newer computer, though I don't remember the specs at all anymore. Picked up a PS1 after my second year, having played games on one (mostly Tenchu and FF7) and on an N64 (mostly Goldeneye) and deciding I liked the lineup for the PS1 more.
Upgraded my computer yet again my third year, I believe to a Pentium 4. Purchased a PS2 as a graduation present to myself when I finished college, as I knew the series that I enjoyed on PS1 would eventually make their way to the newer system.
Upgraded my computer yet again a year or so later once I had a job. Bought a Game Boy Advanced used from an acquaintance. Purchased a PS3 when I managed to get a 20% off discount at the store I was currently working for, again sticking with the system that I believed would support the games I wanted. Picked up a PSP at some point in here as well.
My girlfriend (now wife) had gotten a DS and got me one for my birthday so we could play games together. We also picked up a Wii when an order came into the store I was working at, getting me 10% off the price. When leaving my job in 2009, I built yet another computer using my cashed out vacation pay, which is the one I am still using.
And I bought a PS Vita this past holiday season.
Planning to buy a PS4 at some point, once I can afford it. I still have all my systems (not counting PCs) except for the Coleco-vision/Atari. However the original Game Boy does not work as the screen just shows all black. My SNES works but usually displays such distorted graphics that only a few games are even playable. Everything else still works fine.